高等学校化学学报

高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (6): 1135.

• 研究论文 • 上一篇    下一篇

与二茂铁酰基相连的螺噁嗪的合成、结构及性质

杨素华1,2, 庞美丽1, 郭心富1, 霍晓莲1, 韩杰1, 孟继本1   

  1. 1. 南开大学化学系, 天津 300071;
    2. 赤峰学院化学系, 赤峰 024001
  • 收稿日期:2008-12-09 出版日期:2009-06-10 发布日期:2009-06-10
  • 通讯作者: 庞美丽, 女, 博士, 副教授, 主要从事有机功能化合物研究, E-mail: pangmeili@nankai.edu.cn; 孟继本, 男, 教授, 主要从事有机功能化合物研究, E-mail: mengjiben@nankai.edu.cn
  • 基金资助:

    国家自然科学基金(批准号: 20602020)资助.

Synthesis, Structure and Properties of a Novel Photochromic Dyad Based on Spirooxazine and Ferrocene

YANG Su-Hua1,2 , PANG Mei-Li1*, GUO Xin-Fu1, HUO Xiao-Lian1, HAN Jie1, MENG Ji-Ben1*   

  1. 1. Department of Chemsitry, Nankai University, Tianjin 300071, China;
    2. Department of Chemsitry, Chifeng College, Chifeng 024001, China
  • Received:2008-12-09 Online:2009-06-10 Published:2009-06-10
  • Contact: PANG Mei-Li, ; MENG Ji-Ben
  • Supported by:

    国家自然科学基金(批准号: 20602020)资助.

PDF (PC)

被引次数

10

摘要：

在二环已基碳二亚胺(DCC)存在下, 将9′-羟基螺噁嗪与二茂铁甲酸进行酯化缩合, 合成了一种与二茂铁酰基相连的螺噁嗪衍生物2, 用核磁共振氢谱、碳谱、红外光谱、高分辨质谱和X射线单晶衍射对其结构进行了表征. 化合物2在几种有机溶剂中都表现出了良好的光致变色性质; 通过实验证明了在无冰水浴冷却条件下, 用高压汞灯照射时化合物2在二氯甲烷中表现出的特殊变色性是酸致变色的结果; 同时还研究了化合物2在固体PMMA薄膜中的光致变色性质. 在高压汞灯照射下, 化合物2在二氯甲烷溶液中显示了良好的荧光性. 循环伏安法测定结果表明化合物2具有良好的氧化还原可逆性.

关键词: 螺噁嗪, 光致变色, 荧光, 循环伏安法, 二茂铁

Abstract:

A novel photochromic compound 2 based on spirooxazine and ferrocene residue was synthesized by esterification reaction of 9′-hydroxy spirooxazine and ferrocene carboxylic acid in the presence of DCC. Its structure was characterized by 1H NMR, 13C NMR, IR, HRMS, and X-ray single crystal diffraction. The UV measurement show that compound 2 has good photochromic properties in several organic solvents and good fatigue resistance property. The special property in dichloromethane was proved to be caused by acidichromism when irradiated with high pressure Hg lamp without ice bath. The photochromic property of compound 2 in solid PMMA thin film was also studied. In the acidic condition, or under irradiation with high pressure Hg lamp without ice bath, the dichloromethane solution of compound 2 exhibit a good fluorescence. Additionally, compound 2 show a good reversibility of the redox, which is determined by CV. Ferrocene derivatives have the property of absorbing light, and this property may be helpful to extend the fatigue life of photochromic compounds. Besides, the new compound may posses photo-electromagnetic property owing to the existence of metal ion.

Key words: Spirooxazine, Photochromism, Fluorescence, Cyclic voltammetry, Ferrocene

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